Two new species of Nilssoniopteris of the order Bennettitales, Nilssoniopteris hamiensis Zhao and Deng, new species and Nilssoniopteris crassiaxis Zhao and Deng, new species, are established from the Xishanyao Formation (Middle Jurassic) of Sandaoling Coal Mine in Hami, Xinjiang, China, based on leaf macromorphology and cuticular features. Nilssoniopteris hamiensis n. sp. is characterized by its varied leaf shapes and trichome bases of 1–4 cells on the abaxial epidermis. Nilssoniopteris crassiaxis n. sp. is characterized by its broad midrib (especially near the leaf base) and trichome bases of 1–3 cells on the abaxial epidermis. Both species possess unique venation patterns that are not only simple and free, but also forked and merged to form closed loops. These anastomosing veins are even more complicated in N. crassiaxis n. sp. in that the veins can fork once, twice, or even three times, the forked veins can later merge with each other or with an adjacent vein to form a closed loop, which may later further disjoin. The generic diagnosis of Nilssoniopteris is thus accordingly emended, particularly in the venation pattern. In addition, the stratigraphic and geographical distributions of all 45 Jurassic Nilssoniopteris species worldwide have been summarized and analyzed to better understand their brief evolutionary history, indicating that Nilssoniopteris might be able to grow not only in subtropical regions as the living cycads are, but also in warm climatic regions.